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Why I’m dead inside… - Sept 2024 (#38)

Welcome back to another one! Your dude Brent is still buzzing from the fed dropping rates half a percent. I’d guess its game on from here for most risk assets. Finally, we might get some respite from a long winter! So that begs the question… do you risk it for that biscuit? I’ve done a previous post on figuring out YOUR risk tolerance, but today I’m putting you into MY head to understand how I think about risk… fair warning… when it comes to risk… I’M DEAD INSIDE.

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Motivation

The biggest risk is not taking any risk. In a world that’s changing quickly the only strategy that’s guaranteed to fail is not taking risks.

-Mark Zuckerberg

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Money

So like I said… I’m kinda like… dead inside. What I mean by that is what scares most people just doesn’t scare me… or at least not the same way. Sure there are things that scare me… especially when it comes to money, but due to my past experiences and the framework I operate under there’s a lot that just doesn’t phase me. Once I explain how I think about risk and the experiences I’ve had, you’ll see how I’ve gotten there.

To start I just want to make it clear that SURE, I never want to lose money and I respect money too much to be careless with it. Anywhere I consider investing I research it like a madman. I don’t just research stuff online (I do a ridiculous amount of that for sure) I also try to have conversations with experts in the field on it. I am constantly forming new relationships with people who know more than me in new areas and pumping them for knowledge.

Over the years I’ve naturally grown my risk tolerance through making, and sometimes losing, larger and larger amounts of money. That however isn’t the thing that really gives me the gumption to take on the bigger and scarier deals. When I think long and hard about what REALLY scares me its this:

Fear of regret

Jeff Bezos often talks about working from a Regret Minimization Framework. He constantly aims to do what he’d regret not doing later. That’s what led him to leave a sweet, super high paying job in finance to go sell books on this newfangled thing called the internet. What he says he cares most about… is what his future self would think…

I don’t want to be the guy, who in 10 years, 20 years, 30 years, etc. is full of regrets for not taking chances. I’d rather be the guy who’s past is littered with failures, but can honestly can say to my future self… I went for it. Even when it scared me… If it turns out I just didn’t have it in me for success than so be it, but I don’t want to look back at my past self and see a guy who let fear be in the driver’s seat and dictate how my life turned out.

What would your future self say to you now? Or will your future self be dead inside…. because you’ll be full of regret?

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That’s all folks!

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